IE35908L - Conversion of phosphoramide compounds to benzamide¹¹derivatives - Google Patents
Conversion of phosphoramide compounds to benzamide¹¹derivativesInfo
- Publication number
- IE35908L IE35908L IE711608A IE160871A IE35908L IE 35908 L IE35908 L IE 35908L IE 711608 A IE711608 A IE 711608A IE 160871 A IE160871 A IE 160871A IE 35908 L IE35908 L IE 35908L
- Authority
- IE
- Ireland
- Prior art keywords
- salt
- product
- formula
- substituted
- compound
- Prior art date
Links
- 150000008039 phosphoramides Chemical class 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract 7
- 150000003936 benzamides Chemical class 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- DSPXASHHKFVPCL-UHFFFAOYSA-N 1-isocyanocyclohexene Chemical compound [C-]#[N+]C1=CCCCC1 DSPXASHHKFVPCL-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 229940054066 benzamide antipsychotics Drugs 0.000 abstract 2
- 239000012320 chlorinating reagent Substances 0.000 abstract 2
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 abstract 2
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 abstract 2
- -1 phosphoramide compound Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract 2
- 229960002317 succinimide Drugs 0.000 abstract 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 abstract 1
- YDPNBRVAZXOPLH-UHFFFAOYSA-N 4-amino-5-chloro-2-hydroxybenzoic acid Chemical compound NC1=CC(O)=C(C(O)=O)C=C1Cl YDPNBRVAZXOPLH-UHFFFAOYSA-N 0.000 abstract 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229960004909 aminosalicylic acid Drugs 0.000 abstract 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1353499 Preparing substituted benzamides; substituted phosphoramides SOC D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE-DE-FRANCE and TEIKOKU CHEMICAL INDUSTRY 20 Dec 1971 [21 Dec 1970] 59101/71 Headings C2C and C2P A substituted benzamide of the formula in which A is a C 1 -C 5 alkylene group, X is H or halogen, R 3 is H, OH or C 1 -C 5 alkoxy and R 1 and R 2 are each C 1 -C 5 alkyl, or salt thereof, is obtained by reacting a substituted benzoic acid of the formula: with a novel phosphoramide compound of the formula: or a salt thereof. The reaction is suitably effected by heating the reactants at 50-150 C. in an inert solvent and when the phosphoramide is used in the form of a salt, e.g. the hydrochloride, the product I is also obtained in the form of a salt. Examples are given for the production of substituted benzamides of Formula I in which (a) R 1 and R 2 are each ethyl, X is Cl and R 3 is OCH 3 and OH respectively, (b) R 1 and R 2 are each ethyl and R 3 and X are each H, the product being obtained directly as the hydrochloride by using the phosphoramide in the form of its trihydrochloride and (c) R 1 and R 2 are each ethyl, R 3 is methoxy and X is Br. When R 3 in the product I is OH the product can be converted to the corresponding compound in which R 3 is alkoxy and in one example 2 - methoxy - 4 - amino - 5 - chloro- (N,N-diethylaminoethyl) benzamide is obtained by treating the corresponding 2-hydroxy compound with dimethyl sulphate. Also, when X is H in the product the latter may be converted to the corresponding 5-chloro compound by treatment with a suitable chlorinating agent, e.g. phenyliodine dichloride, iodine trichloride or succinic imide chloride. The products have pharmacological activity. The novel phosphoramides of Formula III are obtained in the form of their trihydrochloride salts by reacting an appropriate N,N- dialkylene diamine, e.g. diethylethylene diamine, with phosphorus oxychloride and the resulting salt can be converted to the free base by adding an alkali to the trihydrochloride salt. 2 - Hydroxy - 4 - amino - 5 - chlorobenzoic acid is obtained by reacting p-aminosalicylic acid with an appropriate chlorinating agent, e.g. phenyl iodine dichloride, iodine trichloride, succinic imide chloride, or cyanuric chloride.
[GB1353499A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45115341A JPS4940459B1 (en) | 1970-12-21 | 1970-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35908L true IE35908L (en) | 1972-06-21 |
| IE35908B1 IE35908B1 (en) | 1976-06-23 |
Family
ID=14660130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1608/71A IE35908B1 (en) | 1970-12-21 | 1971-12-20 | Substituted phosphoramide compounds and their conversion to substituted benzamide derivatives |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS4940459B1 (en) |
| AR (1) | AR195064A1 (en) |
| AT (1) | AT314509B (en) |
| AU (1) | AU459435B2 (en) |
| BE (1) | BE776936A (en) |
| BG (2) | BG19601A3 (en) |
| CA (1) | CA981692A (en) |
| CH (2) | CH548985A (en) |
| CS (1) | CS174172B2 (en) |
| DE (1) | DE2162917B2 (en) |
| ES (1) | ES398146A1 (en) |
| FI (1) | FI55991C (en) |
| FR (1) | FR2118960B1 (en) |
| GB (1) | GB1353499A (en) |
| HU (1) | HU163170B (en) |
| IE (1) | IE35908B1 (en) |
| IL (1) | IL38417A (en) |
| LU (1) | LU64484A1 (en) |
| MC (1) | MC939A1 (en) |
| NL (1) | NL7117522A (en) |
| NO (1) | NO137088C (en) |
| OA (1) | OA03933A (en) |
| PH (1) | PH9783A (en) |
| PL (1) | PL88937B1 (en) |
| RO (1) | RO57372A (en) |
| SE (1) | SE402277B (en) |
| YU (1) | YU35341B (en) |
| ZA (1) | ZA718479B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793871A (en) * | 1972-07-19 | 1973-05-02 | Renfag Sa | PROCESS FOR THE PREPARATION OF N- (1-ETHYL-2- PYRROLIDYLMETYL) -2-METHOXT-5-ETHYLSULFONYL-BENZAMIDE AND ITS ADDITIONAL SALTS |
| BE791677A (en) * | 1972-07-19 | 1973-03-16 | Renfag Sa | PROCESS FOR THE PREPARATION OF N- (DIETHYLAMINOETHYL) -2- METHOXY-5-METHYLSULFONYL-BENZAMIDE |
| CH614709A5 (en) * | 1975-09-25 | 1979-12-14 | Ciba Geigy Ag |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3170955A (en) * | 1958-04-25 | 1965-02-23 | Abbott Lab | Amino and halogen substituted-n-diloweralkylamino-alkyl-benzamides |
| NL281394A (en) * | 1961-07-25 |
-
1970
- 1970-12-21 JP JP45115341A patent/JPS4940459B1/ja active Pending
-
1971
- 1971-12-17 DE DE2162917A patent/DE2162917B2/en active Granted
- 1971-12-17 YU YU3163/71A patent/YU35341B/en unknown
- 1971-12-20 OA OA54443A patent/OA03933A/en unknown
- 1971-12-20 BG BG021828A patent/BG19601A3/en unknown
- 1971-12-20 NL NL7117522A patent/NL7117522A/xx unknown
- 1971-12-20 FI FI3619/71A patent/FI55991C/en active
- 1971-12-20 BE BE776936A patent/BE776936A/en not_active IP Right Cessation
- 1971-12-20 NO NO4695/71A patent/NO137088C/en unknown
- 1971-12-20 CA CA130,611A patent/CA981692A/en not_active Expired
- 1971-12-20 IE IE1608/71A patent/IE35908B1/en unknown
- 1971-12-20 SE SE7116316A patent/SE402277B/en unknown
- 1971-12-20 BG BG019283A patent/BG18860A3/en unknown
- 1971-12-20 GB GB5910171A patent/GB1353499A/en not_active Expired
- 1971-12-20 AR AR239698A patent/AR195064A1/en active
- 1971-12-20 LU LU64484A patent/LU64484A1/xx unknown
- 1971-12-20 PL PL1971152310A patent/PL88937B1/pl unknown
- 1971-12-20 ES ES398146A patent/ES398146A1/en not_active Expired
- 1971-12-20 ZA ZA718479A patent/ZA718479B/en unknown
- 1971-12-20 MC MC964A patent/MC939A1/en unknown
- 1971-12-20 FR FR7145812A patent/FR2118960B1/fr not_active Expired
- 1971-12-21 HU HUSO1027A patent/HU163170B/hu unknown
- 1971-12-21 AT AT1094671A patent/AT314509B/en not_active IP Right Cessation
- 1971-12-21 CH CH103773A patent/CH548985A/en not_active IP Right Cessation
- 1971-12-21 PH PH13132A patent/PH9783A/en unknown
- 1971-12-21 IL IL38417A patent/IL38417A/en unknown
- 1971-12-21 CH CH1866571A patent/CH545273A/en not_active IP Right Cessation
- 1971-12-21 RO RO69131A patent/RO57372A/ro unknown
- 1971-12-21 AU AU37152/71A patent/AU459435B2/en not_active Expired
- 1971-12-21 CS CS8867A patent/CS174172B2/cs unknown
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